WO2004000023A1 - Insect repellents - Google Patents

Insect repellents Download PDF

Info

Publication number
WO2004000023A1
WO2004000023A1 PCT/CH2003/000403 CH0300403W WO2004000023A1 WO 2004000023 A1 WO2004000023 A1 WO 2004000023A1 CH 0300403 W CH0300403 W CH 0300403W WO 2004000023 A1 WO2004000023 A1 WO 2004000023A1
Authority
WO
WIPO (PCT)
Prior art keywords
menthyl ester
ester
carbamic acid
group
atoms
Prior art date
Application number
PCT/CH2003/000403
Other languages
English (en)
French (fr)
Inventor
Markus Gautschi
Original Assignee
Givaudan Sa
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Givaudan Sa filed Critical Givaudan Sa
Priority to AU2003240349A priority Critical patent/AU2003240349B2/en
Priority to JP2004514505A priority patent/JP2006504638A/ja
Priority to EP03729765A priority patent/EP1515610A1/en
Priority to BR0312156-9A priority patent/BR0312156A/pt
Priority to MXPA04012203A priority patent/MXPA04012203A/es
Priority to US10/518,730 priority patent/US20060063764A1/en
Publication of WO2004000023A1 publication Critical patent/WO2004000023A1/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring

Definitions

  • the present invention relates to compounds having insect repellent characteristics and to compositions containing same.
  • insects are known as a nuisance and some insect genera even represent a health hazard. Therefore, many efforts have been made to eradicate or at least to control these pests.
  • One method of insect eradication is through the use of synthetically produced insecticides.
  • certain insect genera may develop resistance to some whilst others have undesirable effects on human and other animal life, such that their use must be strictly regulated or even forbidden.
  • Naturally-occurring substances are also known to display insect repellent properties, for example citronella oil, tolu and Peru balsams, camphor and various eucalyptus.
  • insect repellent properties for example citronella oil, tolu and Peru balsams, camphor and various eucalyptus.
  • Ri and R 2 are independently selected from the group consisting of H; an aliphatic residue having 1 to 20 carbon atoms, or a cycloaliphatic residue having 5 to 14 carbon atoms, or an aliphatic or cycloaliphatic residue aforementioned containing one or more hetero-atoms selected from O, N or S; an aryl or heteroaryl group having from 6 to 14 carbon atoms and wherein hetero-atoms are selected from O, N or S; or any of the afore-mentioned groups substituted with a group selected from, C 1-4 alkyl, C 1-4 alkoxy, C 2-4 alkenyl, aryl or heteroaryl as defined above, aryloxy, amino-, amido-, ester, keto-, hydroxyl, and halogen, e.g. Cl, Br or I, or
  • Ri and R 2 together with the nitrogen atom to which they are attached form a 5- or 6- membered ring that may optionally contain additional hetero-atoms selected from O, N or S.
  • Preferred groups Ri and R 2 may be selected from alkyl, e.g. C 1-4 alkyl, more particularly methyl, ethyl, n or iso propyl, or n or sec butyl, cycloalkyl, e.g. having 5- or 6-carbon atoms or phenyl.
  • R ⁇ and R 2 are those groups provided on the compounds of Example 1 hereinunder.
  • n-butyl-carbamic acid (-)-menthyl ester; iso-butyl-carbamic acid (-)-menthyl ester; diethyl-carbamic acid (-)-menthyl ester; morpholine-4-carboxylic acid (-)-menthyl ester; and 3-[(-)-menthoxy-carbonylamino]-propionic acid ester have interesting insect repellent properties and these compounds form another aspect of the invention.
  • the compounds defined hereinabove display good repellent activity against insects, in particular against cockroaches. At the same they are safe to be applied to the human body, pets and livestock, or on or against surfaces which may be contacted by humans, pets or livestock.
  • the compounds also possess good substantivity, thereby providing long-lasting activity against insect infestations on surfaces to which they are applied.
  • the compounds possess little or no odour, which makes them suitable for use in perfumed compositions. It is possible to use more than one such compound in an application.
  • menthol may be reacted with a chloroformate bearing the groups Ri and R 2 under alkaline conditions in a manner known in the art.
  • the chloroformates are either commercially available or can be synthesised from known starting materials according to synthetic procedures known to the art. Further and more specific information regarding the syntheses of the compounds is set forth in the Examples.
  • an insect repellent composition comprising at least one of the compounds hereinabove described.
  • the amount of compound or compounds employed in said composition may vary widely depending on a number of factors including the nature of the insect infestation that is intended to be treated and the presence or absence of other insect repellent agents in the composition.
  • a compound or mixtures of the compounds is used at levels of from lppm to lOOOppm, although levels outside these limits may also be useful in some cases.
  • compositions containing a compound or mixtures of compounds of the present invention may be applied to objects in need of protection against insects, either directly, in liquid solution or dispersion, as aerosols or air-sprays, or dispersed in a powdered carrier or in a suitable composition.
  • Compositions which may be useful to repel insects are, for example, detergent compositions, cleaning compositions, paints, wallpaper, upholstery and/or rug shampoos, liquid soaps, soap bars, floor polishes, floor waxes and furniture polishes.
  • compositions which are useful to repel insects from the human body are also included in the scope of the present invention and include compositions such as fine fragrances, colognes, skin creams, sun creams, skin lotions, deodorants, talcs, bath oils, soaps, shampoos, hair conditioners and styling agents.
  • compositions of the present invention may comprise a compound or compounds of the present invention in combination with other known insect repellents, including, but not limited to, N,N-diethyl-m-toluamide (DEET), N,N-diethyl-benzamide, menthyl 2- pyrrolidone-5-carboxylate, N-aryl and N-cycloalkyl neoalkanamides, N-lower alkyl neoalkanamides and nepetalactone.
  • DEET N,N-diethyl-m-toluamide
  • N,N-diethyl-benzamide menthyl 2- pyrrolidone-5-carboxylate
  • N-aryl and N-cycloalkyl neoalkanamides N-lower alkyl neoalkanamides and nepetalactone.
  • natural oils known for their insect repellent characteristics. Examples for such oils include, without limiting, e.g.
  • a compound of the present invention or mixtures thereof may also be used in conjunction with at least one insecticide in order to repel insects from one area and toward the location, where the insecticide is applied to avoid the action of the insecticide in a special area, for example in areas containing foodstuffs.
  • they may be formulated with insecticides so that after the repellent activity has diminished the treated area will still not be safe for insects.
  • a compound or mixtures of compounds for use in the present invention may additionally comprise at least one fragrance compound.
  • fragrance compounds may be of natural and/or synthetic origin, examples for such natural and synthetic fragrance ingredients can be found e.g. in "Perfume and Flavour Materials of Natural Origin", S. Arctander, Ed., Elizabeth, N.J., 1960 and "Perfume and Flavour Chemicals", S. Arctander, Ed., Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 1994.
  • compositions may additionally contain solvents.
  • Solvents that may be used are known to those skilled in the art and include ethanol, ethylene glycol, propylene glycol, diethyl phthalate and dimethyl phthalate.
  • a preferred solvent is dimethyl phthalate, which is known for its insect repellent characteristics.
  • compositions of the present invention may comprise other art-recognised ingredients normally used in such formulations. These include antifoaming agents, anti-microbial agents, anti-oxidants, anti-redeposition agents, bleaches, colorants, emulsifiers, enzymes, fats, fluorescent materials, fungicides, hydrotropes, moisturisers, optical brighteners, perfume carriers, perfume, preservatives, proteins, silicones, soil release agents, solubilisers, sugar derivatives, sun screens, surfactants, vitamins and waxes.
  • antifoaming agents include antifoaming agents, anti-microbial agents, anti-oxidants, anti-redeposition agents, bleaches, colorants, emulsifiers, enzymes, fats, fluorescent materials, fungicides, hydrotropes, moisturisers, optical brighteners, perfume carriers, perfume, preservatives, proteins, silicones, soil release agents, solubilisers, sugar derivatives, sun screens, surfactants, vitamins and waxes.
  • Compounds for use in the present invention have useful properties both as contact and vapour repellent. They are superior to various commercial insect repellents in repelling action, especially against German cockroaches, which are considered to be one of the most difficult household pests to control. Due to their low vapour pressure, the compounds are long-lasting on surfaces to which they have been applied. The long-lasting insect repellency may last up to 2-3 weeks after topical application, depending on the concentration used. Furthermore, the compounds are sufficiently stable in compositions being object of the present invention to maintain their insect repellency.
  • compositions for use in the present invention may also be incorporated in various materials during their manufacturing process. Methods for preparing a product comprising a composition according to the present invention by incorporating said composition into the product during extrusion are preferred.
  • compositions formulated according to the present invention are also effective against other insects such as ants, bees, fleas, flies, hornets, mosquitoes, moths, silverfish, and wasps, and against arachnids such as mites, spiders and ticks.
  • mosquitoes which is a known carrier of malaria and transmits also f ⁇ lariasis and encephalitis
  • Culex which is a carrier of viral encephalitis and filariasis
  • Aedes which carries yellow fever, dengue and encephalitis. From the latter genus, the activity against Aedes aegypti is especially important.
  • Products that may benefit from the addition or incorporation of compounds and/or compositions provided by this invention include, but are not restricted to, household products, industrial cleansing products, personal care products, and pet or livestock care products.
  • the invention also provides covering materials especially floor, wall and furniture coverings, fabrics and plastics materials comprising a composition or compounds as hereinabove defined.
  • the invention therefore also provides a method of repelling insects by the application to a substrate of a preparation comprising at least one compound as hereinabove described.
  • IR v ma x, cm “1 , ATR: 3362w, 2959m, 1734s, 1683s, 1530s, 1256s, 1199m, 1177s, 991m.
  • the study was conducted in an air-conditioned laboratory at a temperature of 22° ⁇ 2°C under a normal day/night cycle, using German cockroaches ⁇ Blatella Germanica) of mixed sex and age. The study was conducted over a 3 day period and the repellent effectiveness was assessed 1, 2 and 3 days after cockroach introduction. Test method:
  • One half of a rectangle of laminate 40cm x 30cm was treated at 20 mg/m 2 of a test compound of formula I. This was achieved by soaking a paper wipe ("Rag on a Roll" ca 20cm x 20cm) in a solution of the test compound in ethanol, squeezing out the excess liquid and wiping over the surface to give the required coverage. This was checked by weighing the cloth after application. The surface was allowed to dry. The other half of the rectangle was wiped with ethanol alone (untreated surface).
  • the treated laminate rectangle was placed on the bench and a plastic container was placed on the rectangle. This had been treated with "Fluon” (trade mark), a sprayable fmoropolymer, to prevent cockroach escape.
  • Two sheets of laminate (10cm x 10cm) were placed on the laminate, one on the treated surface and one on the untreated surface. This acted as a cockroach harbourage.
  • the laminate sheet to be used in the treated section was treated at the same rate as the treated laminate.
  • the laminate was placed on two 1cm high bottle tops to allow cockroaches access under the laminate.
  • Example 2 The methodology of Example 2 was repeated for all of the compounds set forth in Example 1. The results are presented in the following table.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/CH2003/000403 2002-06-21 2003-06-20 Insect repellents WO2004000023A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
AU2003240349A AU2003240349B2 (en) 2002-06-21 2003-06-20 Insect repellents
JP2004514505A JP2006504638A (ja) 2002-06-21 2003-06-20 昆虫忌避剤
EP03729765A EP1515610A1 (en) 2002-06-21 2003-06-20 Insect repellents
BR0312156-9A BR0312156A (pt) 2002-06-21 2003-06-20 Repelentes de insetos
MXPA04012203A MXPA04012203A (es) 2002-06-21 2003-06-20 Repelente de insectos.
US10/518,730 US20060063764A1 (en) 2002-06-21 2003-06-20 Insect repellents

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0214342.8 2002-06-21
GBGB0214342.8A GB0214342D0 (en) 2002-06-21 2002-06-21 Insect repellents

Publications (1)

Publication Number Publication Date
WO2004000023A1 true WO2004000023A1 (en) 2003-12-31

Family

ID=9939035

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CH2003/000403 WO2004000023A1 (en) 2002-06-21 2003-06-20 Insect repellents

Country Status (9)

Country Link
US (1) US20060063764A1 (enrdf_load_stackoverflow)
EP (1) EP1515610A1 (enrdf_load_stackoverflow)
JP (1) JP2006504638A (enrdf_load_stackoverflow)
CN (1) CN100338034C (enrdf_load_stackoverflow)
AU (1) AU2003240349B2 (enrdf_load_stackoverflow)
BR (1) BR0312156A (enrdf_load_stackoverflow)
GB (1) GB0214342D0 (enrdf_load_stackoverflow)
MX (1) MXPA04012203A (enrdf_load_stackoverflow)
WO (1) WO2004000023A1 (enrdf_load_stackoverflow)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006523244A (ja) * 2003-04-14 2006-10-12 ジボダン エス エー フレグランスとして有用なカルバメート類
EP2135516A1 (de) 2008-06-13 2009-12-23 Symrise GmbH & Co. KG Neo-Menthylderivate als Geschmacksstoffe
WO2010149798A2 (en) 2010-06-14 2010-12-29 Symrise Ag Use of polyols for enhancing the cooling effect of a cooling substance and cooling mixtures having an enhanced cooling effect
WO2011061330A2 (de) 2009-11-20 2011-05-26 Symrise Ag Verwendung physiologischer kühlwirkstoffe und mittel enthaltend solche wirkstoffe
EP2389922A1 (en) 2010-05-25 2011-11-30 Symrise AG Cyclohexyl carbamate compounds as anti-ageing actives
US20120014884A1 (en) * 2009-04-01 2012-01-19 Colgate-Palmolive Company Menthol-derivative compounds and use thereof as oral and systemic active agents
WO2013041621A1 (de) 2011-09-20 2013-03-28 Basf Se Niedermolekulare modulatoren des kälte-menthol-rezeptors trpm8 und deren verwendung
US8710096B2 (en) 2008-08-26 2014-04-29 Basf Se Detection and use of low molecular-weight modulators of the cold-menthol receptor TRPM8
WO2014095541A1 (en) 2012-12-20 2014-06-26 Henkel Ag & Co. Kgaa Insect repellent cleaning composition
US9029415B2 (en) 2010-06-14 2015-05-12 Symrise Ag Cooling mixtures with an enhanced cooling effect of 5-methyl-2-(propane-2-yl)cyclohexyl-N-ethyloxamate
WO2019043164A1 (de) 2017-08-31 2019-03-07 Basf Se Verwendung physiologischer kühlwirkstoffe und mittel enthaltend solche wirkstoffe
WO2022207944A2 (en) 2022-07-11 2022-10-06 Symrise Ag Novel mixtures and uses of (2e)-3-(1,3-benzodioxol-5-yl)-n-phenyl-n-(tetrahydro-3-furanyl)-2-propenamide

Families Citing this family (4)

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Publication number Priority date Publication date Assignee Title
EP2064959B1 (de) * 2007-10-31 2012-07-25 Symrise AG Aromatische Neo-Menthylamide als Geschmacksstoffe
US8911715B2 (en) * 2008-05-30 2014-12-16 Symrise Ag L-menthyl-N-(2-hydroxyphenyl)carbamate
US20110294876A1 (en) * 2010-05-25 2011-12-01 Symrise Ag Cyclohexyl carbamate compounds as anti-ageing actives
US20130324522A1 (en) * 2010-12-17 2013-12-05 The Rockefeller University Insect odorant receptor antagonists

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DE1518713B1 (de) * 1965-07-13 1971-01-14 Degussa Verfahren zur Herstellung von Terpenestern
JPS60199804A (ja) * 1984-03-26 1985-10-09 Nippon Kayaku Co Ltd 有害生物忌避剤
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Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006523244A (ja) * 2003-04-14 2006-10-12 ジボダン エス エー フレグランスとして有用なカルバメート類
EP2135516A1 (de) 2008-06-13 2009-12-23 Symrise GmbH & Co. KG Neo-Menthylderivate als Geschmacksstoffe
US8852664B2 (en) 2008-06-13 2014-10-07 Symrise Ag Neo-menthyl derivatives as flavor materials
EP3115045A2 (de) 2008-08-26 2017-01-11 Basf Se Nachweis und verwendung niedermolekularer modulatoren des kälte-menthol-rezeptors trpm8
EP3698779A1 (de) 2008-08-26 2020-08-26 Basf Se Nachweis und verwendung niedermolekularer modulatoren des kälte-menthol-rezeptors trpm8
US9346823B2 (en) 2008-08-26 2016-05-24 Basf Se Detection and use of low molecular-weight modulators of the cold-menthol receptor TRPM8
EP3103447A1 (de) 2008-08-26 2016-12-14 Basf Se Nachweis und verwendung niedermolekularer modulatoren des kälte-menthol-rezeptors trpm8
US8710096B2 (en) 2008-08-26 2014-04-29 Basf Se Detection and use of low molecular-weight modulators of the cold-menthol receptor TRPM8
US20120014884A1 (en) * 2009-04-01 2012-01-19 Colgate-Palmolive Company Menthol-derivative compounds and use thereof as oral and systemic active agents
US10426752B2 (en) * 2009-04-01 2019-10-01 Colgate-Palmolive Company Menthol-derivative compounds and use thereof as oral and systemic active agents
WO2011061330A2 (de) 2009-11-20 2011-05-26 Symrise Ag Verwendung physiologischer kühlwirkstoffe und mittel enthaltend solche wirkstoffe
EP3663366A2 (de) 2009-11-20 2020-06-10 Symrise AG Verwendung physiologischer kühlwirkstoffe und mittel enthaltend solche wirkstoffe
DE102010002558A1 (de) 2009-11-20 2011-06-01 Symrise Ag Verwendung physiologischer Kühlwirkstoffe und Mittel enthaltend solche Wirkstoffe
EP2389922A1 (en) 2010-05-25 2011-11-30 Symrise AG Cyclohexyl carbamate compounds as anti-ageing actives
US9029415B2 (en) 2010-06-14 2015-05-12 Symrise Ag Cooling mixtures with an enhanced cooling effect of 5-methyl-2-(propane-2-yl)cyclohexyl-N-ethyloxamate
EP3434330A1 (en) 2010-06-14 2019-01-30 Symrise AG A method for enhancing the cooling effect of a cooling compound
EP2394703A1 (de) 2010-06-14 2011-12-14 Symrise AG Kühlmischungen mit verstärkter Kühlwirkung von 5-Methyl-2-(propan-2-yl)cyclohexyl-N-ethyloxamat
WO2010149798A2 (en) 2010-06-14 2010-12-29 Symrise Ag Use of polyols for enhancing the cooling effect of a cooling substance and cooling mixtures having an enhanced cooling effect
WO2013041621A1 (de) 2011-09-20 2013-03-28 Basf Se Niedermolekulare modulatoren des kälte-menthol-rezeptors trpm8 und deren verwendung
WO2014095541A1 (en) 2012-12-20 2014-06-26 Henkel Ag & Co. Kgaa Insect repellent cleaning composition
WO2019043164A1 (de) 2017-08-31 2019-03-07 Basf Se Verwendung physiologischer kühlwirkstoffe und mittel enthaltend solche wirkstoffe
US11434220B2 (en) 2017-08-31 2022-09-06 Basf Se Use of physiological cooling active ingredients, and compositions comprising such active ingredients
WO2022207944A2 (en) 2022-07-11 2022-10-06 Symrise Ag Novel mixtures and uses of (2e)-3-(1,3-benzodioxol-5-yl)-n-phenyl-n-(tetrahydro-3-furanyl)-2-propenamide

Also Published As

Publication number Publication date
CN100338034C (zh) 2007-09-19
GB0214342D0 (en) 2002-07-31
BR0312156A (pt) 2005-03-29
AU2003240349B2 (en) 2008-03-06
MXPA04012203A (es) 2005-02-25
AU2003240349A1 (en) 2004-01-06
US20060063764A1 (en) 2006-03-23
EP1515610A1 (en) 2005-03-23
JP2006504638A (ja) 2006-02-09
CN1662141A (zh) 2005-08-31

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